Triethylamine → N-4-cyanobenzoyl-beta-m-chlorophenyl-alpha,alpha-dimethyl-beta-alanyl-4-piperidineacetic acid methyl ester

HRID 361752ノート

反応式

HRID 361752 の反応式
[C:1]([C:3]1[CH:25]=[CH:24][C:6]([C:7]([NH:9][CH:10]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=2)[C:11]([CH3:16])([CH3:15])[C:12](O)=[O:13])=[O:8])=[CH:5][CH:4]=1)#[N:2].CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.[CH3:60][O:61][C:62](=[O:70])[CH2:63][CH:64]1[CH2:69][CH2:68][NH:67][CH2:66][CH2:65]1>C(Cl)Cl>[CH3:60][O:61][C:62](=[O:70])[CH2:63][CH:64]1[CH2:65][CH2:66][N:67]([C:12](=[O:13])[C:11]([CH3:15])([CH3:16])[CH:10]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=2)[NH:9][C:7](=[O:8])[C:6]2[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:25][CH:24]=2)[CH2:68][CH2:69]1

参加物

6

反応物 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 1515259Methyl 4-piperidineacetateHCID 10713311N-4-Cyanobenzoyl-beta-m-chlorophenyl-alpha,alpha-dimethyl-beta-alanine

生成物 1

HCID 10791393N-4-cyanobenzoyl-beta-m-chlorophenyl-alpha,alpha-dimethyl-beta-alanyl-4-piperidineacetic acid methyl ester収率 65%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

N-4-Cyanobenzoyl-β-m-chlorophenyl-α,α-dimethyl-β-alanine (300 mg, 0.84 mmol) was dissolved in methylene chloride (30 ml). To the resulting solution, BOP reagent (409 mg, 0.92 mmol) and triethylamine (1 ml) were added under cooling with ice and the mixture was stirred for 30 minutes. To the reaction mixture was added 4-piperidineacetic acid methyl ester (572 mg, 3.36 mmol) and the resulting mixture was stirred overnight. After the solvent was distilled off, the residue was applied to a silica gel column (2.2×20 cm) and eluted with a mixed solution (hexane:ethyl acetate=3:1). The desired fractions were collected and the solvents were distilled off to yield an oil of N-4-cyanobenzoyl-β-m-chlorophenyl-α,α-dimethyl-β-alanyl-4-piperidineacetic acid methyl ester (270 mg, 65.0%).

後処理

  1. temperatureunder cooling with ice
  2. stirringthe resulting mixture was stirred overnight
  3. distillationAfter the solvent was distilled off
  4. washeluted with a mixed solution (hexane:ethyl acetate=3:1)
  5. customThe desired fractions were collected
  6. distillationthe solvents were distilled off

出典と根拠

ORDレコード
ord-173b1748aa564d3fa2765318a8d9b901
出典データセット
uspto-grants-1999_02
特許番号
US05866592

反応ノート

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